Potassium Carbonate → 2-(1-{[4-chloro-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-yl)-1H-isoindole-1,3(2H)-dione

HRID 1946330노트

반응식

HRID 1946330 반응식
[NH:1]1[CH:5]=[CH:4][C:3]([N:6]2[C:14](=[O:15])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]2=[O:16])=[N:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=1[C:32]([F:35])([F:34])[F:33]>CN(C=O)C.C(Cl)Cl.O.[Cl-].[Na+].O>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][N:1]2[CH:5]=[CH:4][C:3]([N:6]3[C:14](=[O:15])[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[C:7]3=[O:16])=[N:2]2)=[C:26]([C:32]([F:33])([F:34])[F:35])[CH:27]=1

참가 물질

8

반응물 3

HCID 11430Potassium CarbonateHCID 34925974-Chloro-2-(trifluoromethyl)benzyl bromideHCID 178514958HCID 178514958, 화합물

생성물 1

HCID 667707212-(1-{[4-chloro-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-yl)-1H-isoindole-1,3(2H)-dione

시약·촉매·용매 4

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 57417360Sodium chloride; water용매

실험 절차

A mixture of 2-(1H-pyrazol-3-yl)-1H-isoindole-1,3(2H)-dione (for a preparation see Intermediate 28)(3 g, 14.1 mmol) and potassium carbonate (2.92 g, 21.1 mmol) in DMF (30 ml) was stirred under nitrogen at ambient temperature for 5 min. To the pale yellow suspension was added 1-(bromomethyl)-4-chloro-2-(trifluoromethyl)benzene (3.85 g, 14.07 mmol, Alfa Aesar). The mixture turned to a colourless suspension. The reaction mixture was stirred at ambient temperature under nitrogen overnight. The reaction mixture was diluted with DCM (50 ml) and water (50 ml). To the emulsion was added brine (30 ml). The resulting phases were separated and the aqueous layer further extracted with DCM (50 ml). The combined organic extracts were filtered through a hydrophobic frit and the solvent removed in vacuo to give 2-(1-{[4-chloro-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-yl)-1H-isoindole-1,3(2H)-dione (6.14 g) as an off-white gum.

후처리

  1. stirringThe reaction mixture was stirred at ambient temperature under nitrogen overnight
  2. customThe resulting phases were separated
  3. extractionthe aqueous layer further extracted with DCM (50 ml)
  4. filtrationThe combined organic extracts were filtered through a hydrophobic frit
  5. customthe solvent removed in vacuo

출처 및 근거

ORD 기록
ord-2aa50f8131144cafb6420e1f8910a2a3
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399436B2

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